Grandma's Mason Jar: For the beginner this is probably the easiest way to take rose cuttings. Not much equipment is needed, just a clear quart-size glass jar and some cuttings from your favorite rose. For you modern sodapop lovers, a 2-liter plastic bottle with the bottom cut off will work just as well. Cut a piece of rose stem about 6 inches long, remove the bottom set of leaves, and just stick the stem into the ground (or into a pot) a couple inches deep, and cover with a jar or bottle. You will need to periodically water the soil around the jar, otherwise the rose stem will dry out. It will take a couple of months for the rose stem to take root and begin leafing out with its new growth. The best time of year is spring or early fall. If you live in a mild climate, then winter and summer can also be successful for rooting roses. Intense summer heat of 100 degrees is not conducive for taking rose cuttings, nor are 32 degree or below winters.
Allow rose hips to develop by leaving dead flowers on the plant. The flowers are typically pollinated by insects, or pollinate themselves in some varieties, so there is no need to pollinate by hand unless you are breeding specific plants together. Leave the flowers on the rose plant without cutting them. After they wither, small fruits known as rose hips will develop in their place.
There will be disappointments along the way, when many rose seeds fail to germinate, or perhaps they do germinate, only to die several weeks later from damp-off disease. Sometimes a rose seedling will turn out to be as ugly as sin, or very sickly, and you will reluctantly have to throw it away. Other times they will be just ho-hum, or look too much like its parent, and therefore have no value. But, just when you don't expect it, you might discover that one of your rose seedlings turns out to be very special.